Formic Acid → HCID 117735920, compound

HRID 1482275Notes

Reaction equation

HRID 1482275 reaction equation
[C:1](=[O:23])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[N+:11]=[N-:12])=[CH:6][CH:5]=1.[S:24]1[CH2:28][C@@H:27]([C:29]([OH:31])=[O:30])[NH:26][CH2:25]1.C(N(CC)CC)C.C(O)=O>CN(C)C=O>[N:10]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][O:2][C:1]([N:26]2[C@H:27]([C:29]([OH:31])=[O:30])[CH2:28][S:24][CH2:25]2)=[O:23])=[CH:9][CH:8]=1)=[N+:11]=[N-:12]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 93176L-ThioprolineHCID 11809184HCID 11809184, compound

Product 1

HCID 117735920HCID 117735920, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Azidobenzyl (4-nitrophenyl) carbonate prepared by a method known in the literature (Bioconjugate Chem. 2008, 19, 714) (3.50 g, 11.1 mmol) was added to a solution of (R)-thiazolidine-4-carboxylic acid (H-Thz-OH) (Compound SP609) (1.48 g, 11.1 mmol) and triethylamine (Et3N) (4.66 ml, 33.4 mmol) in Dimethylformamide (DMF) (11.0 ml) at 0° C. under a nitrogen atmosphere, and the mixture was stirred at room temperature for 19 hours. Formic acid (2.1 ml) was added to the reaction solution, and the mixture was purified by reverse-phase silica gel chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution) to afford (R)-3-(((4-azidobenzyl)oxy)carbonyl)thiazolidine-4-carboxylic acid (Acbz-Thz-OH) (Compound SP610) (3.17 g, 92%).

Workup

  1. customthe mixture was purified by reverse-phase silica gel chromatography (0.1% aqueous formic acid solution/0.1% formic acid-acetonitrile solution)

Sources & evidence

ORD record
ord-df2a64dd89334a16b3e12deff488a130
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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